


Shenanigans

by CatherineMorgenstern



Series: TWD Smut [5]
Category: The Walking Dead & Related Fandoms, The Walking Dead (TV)
Genre: Dirty Talk, F/M, Orgasm Control, Orgasm Delay/Denial, Vaginal Fingering, brief case of sexual harassment (reader's bum is grabbed), mild choking, others are asleep in the room during sex, shameless use of bedsharing trope, unprotected sex (wrap it up kids)
Language: English
Status: Completed
Published: 2017-10-04
Updated: 2017-10-04
Packaged: 2019-01-08 23:14:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,873
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12264066
Author URL: https://archiveofourown.org/users/CatherineMorgenstern/pseuds/CatherineMorgenstern
Summary: Having to stay the night at an outpost was so not what you had in mind, but Simon manages to make it worth your while.





	Shenanigans

**Author's Note:**

> This is a scenario taken straight out of my friend's fantasies. I've had the worst case of writer's block with this, so I hope you enjoy it. 
> 
> A million thanks to my outstanding beta, [Heeley](http://archiveofourown.org/users/Heeley/pseuds/Heeley).
> 
> For those of you who want to skip ahead to the juicy bits, it's pretty much the halfway point (I've put a divider there).

Taking in the dull, dimly lit walls of the outpost and it's dirty grey floors, you couldn't help but make a face. Distracted by your perusal, you almost crashed into Simon's broad back, who was talking to the man in charge. The Sanctuary never looked this shabby and you didn't fancy having to stay here one bit. Not even for a night.

Your group had been on your way back home after having paid Hilltop a visit to collect their weekly dues when a herd of walkers had cut three of jeeps off from the trucks preceding them. After Simon had talked to Negan on the walkie, he'd ordered you to drive to the nearest outpost as it was getting dark and that damn herd only seemed to get bigger while the rest headed to the Sanctuary, bringing the collected goods with them.

Now here you were in this dank outpost that housed only men that weren't good enough to stay at the Sanctuary. The look you’d received from those who'd welcomed you inside, had caused you to grit your teeth in disgust and exchange a sneering look with Arat and Laura. Apparently, the scum - you refused to call these poor excuses for men Saviors - hadn't seen women in as long as they'd been stationed here.

Fucking. Great.

You were way too tired and pissed off to deal with them. Hell, you'd take Dwight’s aggravating company over any of theirs and that was saying a lot.

The dude in charge, Pete, sported a smile that made you uneasy. He was the epitome of a sleazeball and his overall demeanor raised the hairs at the back of your neck. Even though you knew how to handle yourself, especially when push came to shove, you found yourself inching closer to Simon a bit, causing Negan's right-hand man to throw you a brief look over his shoulder that almost embarrassed you before you caught Dwight regarding Pete with utter contempt. If even Dwighty-boy picked up on him being weird as fuck, there must be something seriously wrong with Pete.

“I'm sure you guys would like to get something to eat before getting cleaned up and hitting the sacks,” the sleazeball said in a nasally voice.

“Damn straight,” Simon replied, clapping Pete on the back with a bright grin that was so fake, it made Arat audibly snort. “Lead the way, my friend.”

Letting yourself fall back far enough to walk next to Arat, you followed the others towards what was hopefully a well-stocked kitchen.

“You getting the same vibe from the douche as I am?” you asked Arat in a whisper.

“Yeah,” Arat hissed, “the fucker has rapist written all over him, if you ask me.”

“It'd be wise to stick with our group then,” Laura joined in. “No need to make new, unwanted friends.”

“I'm so with you on that. The lot of them give me the creeps. I wish that damned herd hadn't cut us off,” you replied as you turned a corner before adding wistfully, “ we could be in our own beds by now.”

“Ladies,” Simon's booming voice interrupted. ”Care to join us or are yer lot plannin’ on havin’ a picnic over there?”

Rolling your eyes at the other women, you stepped into a smallish room that served as the cafeteria, judging by the amount of tables strewn throughout. Your musings were cut short by a heavenly scent wafting over from pots that were being carried in right now. Your stomach growled. Christ, you were hungry. A quick sweep of the room told you there weren't enough free seats next to each other to sit with Arat and Laura, so, without further ado, you sat down between David and Dwight. Normally, that would be far from your first choice but it was the only seat left at the table that already had a meal set in its midst. Besides, you figured being at the same table as Simon might result in some preferential treatment as far as food was concerned.

After scowling at David, your least favourite Savior, and elbowing Dwight out of sheer spite, you scooped a generous amount of thick stew onto your plate and grabbed a bread roll. Since the guys around you had already started eating, you dug in with gusto. Admittedly, the stew turned out to taste just as good as it had smelled; the first good thing in this hellhole.

At one point, the local guy sitting opposite you tried to start a conversation, but you completely ignored him in favour of getting a second helping, uninterested in faking enthusiasm to get to know any of them.

Once you were done, you looked to Simon who hadn't yet finished his meal, making light-hearted conversation with your hosts. Not wanting to draw any unnecessary attention to yourself, you quietly waited for him to get up, so Pete would finally show you where the bath- and bedrooms were located.

“Ah, that was good. Yer ‘ave our thanks,” Simon said. “If you'd be so kind as to show us where we might clean up and sleep now?”

“Of course, of course,” Pete replied in a downright simpering tone. “Unfortunately, we only have space for one or two of you in various rooms. But we pulled some beds from storage the minute Negan contacted us about your arrival, which we put in an empty room. Some of you will have to share, though, I'm afraid. This outpost isn't meant to hold many guests.”

“That's quite alright, we'll manage,” Simon said, good-naturedly.

“Great!” Pete said before grinning lecherously and adding, “I'm sure some of my men would be delighted to share their beds with any one of your lovely ladies.”

You stilled and snapped your gaze to Simon. The audacity of that creep!

Simon's smile grew tight. “No need, the female _Saviors_ will be with me.”

The emphasis he put on _Saviors_ was an unmistakable warning to the others and you couldn't suppress the smug grin forming on your lips. Leave it to Simon to establish boundaries.

After leading the way to the communal bathroom - the look Arat sent you said _no way are we gonna shower with the dudes_ -, Pete led you to the aforementioned spare room. Peeking inside, you were met with the sight of three single beds crammed so close together there was barely enough space between them to get comfortably in and out.

“So we got six free beds in various rooms. Regrettably, that leaves five of you to make do with this,” he said before adding in a joking tone, “unless someone would like to crawl into mine.”

“Hey?!” you screeched as you felt a pinch on your bum before grabbing the offending hand by the wrist to jerk it away from you. “Whose hand is this?”

The sleazeball's surprised face at being caught was evidence enough. Before you could make up your mind on how to punish him, you found yourself staring at Pete choking and spluttering.

Simon had reacted immediately and smacked the idiot into the wall, holding him by the throat with his corded forearm. The height difference caused Simon to lean down before he said in a deceptively soft voice, “I thought I'd made myself clear? I know yer lot haven't stayed at the Sanctuary for ages, but I'm sure yer can't ‘ave forgotten about Negan's rules? If yer ‘ave, I'd ‘ave to tell the boss about it and lemme tell ya that won't end pretty for yer if he'll ‘ave to come out here to teach yer a much needed lesson. I doubt any of yer would like to ‘ave a meeting with Lucille. Am I right?”

You had crossed your arms and were staring Pete down with a murderous look on your face. Truth be told, it took a lot of effort to not outright grin at Simon putting the creep in his place. You can say what you want about Negan and his Saviors, but any type of sexual harassment was a big no-no, which had been the main selling point to join for you.

“Now, if any of yer make advances on any of the ladies again without their explicit invitation, you'll leave me no choice but to put yer down myself. Understood?”

Pete's face was turning a delightful shade of red as he tried to tell Simon that he got it now.

“Great!” Simon exclaimed with that same fake grin from earlier.

Letting the useless piece of shit sink to the floor as he abruptly stepped away, Simon turned to the three women. “You're stayin’ ‘ere with me,” he barked before turning to the rest of their group with his hands on his hips. “One more of yer gotta join and then good ole Pete ‘ere will show the rest of you to the other free beds.”

Without so much as a peep, Dwight stepped into the room and you rolled your eyes in distaste. Of course it had to be Dwighty-boy.

Once inside, Laura brought up the issue of wanting to clean up after the long day you've had. Simon agreed to let the women go first and ordered Dwight to stand guard outside.

Taking the towels that had been stacked on one of the beds, you made your way to the communal bathroom.

You gave Dwight a warning look. “Don't even think about sneaking a peek,” you snapped at him.

“Don't worry your pretty little head, sunshine. You're not as irresistible as you might think,” he replied with a scoff as he leaned against the wall.

“Maybe, but beggars are seldom choosers,” you said before you slammed the door in his face.

The shower did wonders for your mood. If you could have, you would've stayed under the hot sprays for hours. But knowing what a luxury warm water was, you couldn't bring herself to use up too much of it. Even though Pete the douche would've deserved an icy surprise.

The only drawback was having to put your old clothes back on. But at least they'd only been worn today.

Arat and Laura swiftly chose the bed at the far left. You were slightly annoyed that they didn't even talk about who would be sharing a bed with whom. Then again, the two of them were much closer friends with each other than with you.

Deciding to take the bed at the far right, so you wouldn't have to sleep in the middle, leaving you surrounded by multiple people at all sides, you were faced with the dilemma of what to wear to bed. Pyjamas weren't exactly an option but your top wasn't even long enough to fall to the tops of your thighs.

It was no use as you refused to sleep with your trousers on. Sleeping in the same room with four other people would make the temperature rise anyway. Before you could dither any longer, you took off your shoes, socks, trousers and bra and quickly hopped under the covers.

Simon and Dwight were back a few minutes later, stopping just past the threshold. Their eyes darted from you to the empty middle bed to each other. A smirk tugging at the corner of Simon's mouth made his mustache twitch.

“Sooooo … who'd you like to cuddle with tonight, dove?” he asked you with barely concealed amusement, waggling his eyebrows comically.

“One of you could always be a gentleman and sleep on the floor,” you said hopefully.

“No dice,” Simon replied and you weren't delusional enough to assume Dwight would ever show even a resemblance of manners when it came to you.

“So? Who's it gonna be?”

Even if you hadn't already despised Dwight, the leer he gave you at that would've made the decision for you.

“In what world do you think I'd ever choose Dwight?” you spat, giving Dwight a disgusted look.

Simon grinned in response and walked over to the sound of Dwight mumbling an insult, no doubt.

He stood at the end of the bed, taking off his clothes without a care in the world. Well, anyone who looked like that had no need to feel self-conscious, you supposed. You couldn't help but admire his toned body as he stripped down to only black briefs and an undershirt.

“Yer gonna scoot over or do yer need more time to ogle me?”

Snapping your eyes up to Simon's, you couldn't keep the blush from reddening your cheeks.

“Uhm, would you mind sleeping next to the wall? It makes me feel claustrophobic when I'm caged in on both sides without an easy exit,” you admitted tentatively.

“Sure thing,” he replied and raised his eyebrows when you made no move whatsoever to get out of bed. “Yer gonna make me jump over you?”

“What?” you stammered. “Oh! No, of course not. But, uhm, turn around. Please?”

He sighed, but did as he was told. “You're a lotta work, ain't ya, sweets?”

“Hardly,” you huffed out, sounding annoyed. “I just don't fancy prancing around in my underwear.”

Turning to the side without looking at you, he grabbed his discarded shirt and threw it at your face. “Here.”

You looked at him in surprise. “Thanks.”

Somehow you managed to take off your top without flashing the other occupants of the room and buttoned up Simon's shirt that fell to the middle of your thighs. Much better.

“Okay, you can turn around now.”

“Took yer long enough,” he teased as he climbed into bed.

You didn't even grace his comment with an answer before following after him.

After a few minutes of shuffling and some elbows to various body parts, the two of you realised the bed was a tad too small to sleep back to back. As Dwight shuffled to turn off the light, you figured out that the only position that was somewhat comfortable resulted in him spooning you.

His right arm stretched out above your head to dangle off the bed and his left came to rest around your waist with his chest pressed along your back. You could've fried an egg on your face, judging by how warm your cheeks suddenly felt.

Not that you were complaining. You'd been harbouring a crush on Negan's right-hand man for a while now. But this wasn't exactly how you'd imagined to come into close contact with him.

Settling down, you closed your eyes and started to feel drowsy pretty fast. It had been a very long day. The feeling of Simon's lips and soft breath at the back of your head made you snuggle into the pillow before you drifted off, breathing in his clean scent that had a hint of citrus to it.

* * *

When you woke up it was in the middle of the night to a weight pressing you down. It seemed as though Simon had thrown his leg across your thigh in his sleep. The coarse hairs on his leg raised goosebumps on your smooth skin. His arm was still across your waist but had shifted so that his hand was almost cupping your breast. Your breath caught in your throat and you tried to wriggle free of his tight hold without waking him.

As you attempted to scoot upwards so his hand would slip to safer territory, you must've arched your back because your arse was suddenly pressed against his crotch and a very obvious bulge.

Gulping, you wriggled to put some space between your bodies when his arm tightened around you.

“If yer don’t stop doing that, you’re gonna ‘ave to take care of it for me,” Simon mumbled sleepily with a shallow roll of his hips.

The feeling of him hard and ready made you moan. Embarrassed, you slapped a hand across your mouth, praying to all the gods above and below that the others hadn't noticed anything.

A low chuckle raised the hairs on the back of your neck as Simon pulled you even tighter against him and began to draw little circles across your ribs.

“Did yer just moan for me, dove?” he taunted deviously.

“Shut up,” you hissed. “I'm not the one with the rather obvious problem.”

He chuckled again. “Natural reaction to ‘aving a beautiful woman pressed against me.”

You rolled your eyes. “Don't try to sweet talk me.”

He trailed his hand down your stomach before slipping it under the shirt to slowly drag his calloused fingertips up over your bare skin, drawing a line from just above your panties to right under your breasts. The action made you bite your lip and shudder involuntarily.

When you didn't tell him to stop or try to pull away, he shifted you slightly so that your head was on his arm against his shoulder before starting to massage your breast.

You found yourself rocking back against him as he sucked on your neck and brushed your nipple, the sensations shooting straight down to your core, dampening your panties.

Switching to the other breast to coax that nipple into an equally hard peak, he licked up your neck before nipping your earlobe. He kept tugging and rolling your sensitive buds, alternating between them.

“I've been admiring these for a while now,” he admitted hotly. “Glad you finally let me get my hands on you.”

His words made you grin through the soft moan he drew from you. The sound of your pleasure caused Simon to slowly start thrusting against your bum. You had to bite down on your hand to stop yourself from making any more embarrassing sounds.

You could feel him smile against the delicate skin behind your ear. His mustache tickled slightly and you squirmed before he pressed open-mouthed kisses, interspersed with sharp nips, along the column of your exposed neck. A particularly hard bite was placed on your pulse point before his tongue soothed the sting, ending in a kiss.

Ceasing his ministrations on your now hard nipples, his leg drew back for a second only to settle between yours, spreading you for him under the cover of the blanket. His hand slid to the apex of your thighs to rub slowly up and down your clothed slit.

Your stomach quivered with the effort not to cry out at his pleasurable ministrations.

Leisurely, he rubbed you through your soaked panties that were moulded to your wet sex by now. The way he circled your clit with the fabric as a barrier made you wish for the feel of skin on skin. But Simon wasn't ready to comply just yet. Instead, he started to push the material just past your clenching entrance with his index finger, earning a desperate little mewl from you.

“Yer like this, dove? Hmmm?” he breathed into your ear. “Want me to fuck yer with Dwighty-boy a few feet away?”

Whimpering, you nodded frantically.

“Yer want me to put my fingers in yer needy little cunt?” he taunted.

“Gods,” you breathed out. “Yes!”

“Beg.”

“Please, Simon!”

“I'm sure yer can do better than that. What do yer want from me?” he goaded.

“Simon!” you pleaded, trying to keep your voice to a whisper. “Please. I want to feel your fingers inside me, please!”

Humming in satisfaction, his digits slipped beneath the elastic of your underwear.

He buried his face in your hair and groaned.

“Jesus fucking Christ, you're so wet,” he growled as he fondled you. “This all for me?”

“Yes, Simon,” you whispered feverishly. “Please!”

“Since you said please so nicely,” he murmured, forcing two thick fingers into you as his thumb settled on your clit to rub harshly back and forth.

A moan slipped out at his sudden force and Simon clamped his unoccupied hand over your mouth. After thrusting his fingers in and out a few times so slowly it bordered on torture, he soon pushed another into you.

As you bucked your hips with a muffled whimper, he told you in a soothing voice, “Gotta open yer up a bit first. Think yer can 'andle that?”

Trying to get used to the stretch and relax your muscles, it still felt like too much and not enough at the same time.

The combination of his painfully pleasurable fingers and the way he was rubbing his clothed erection against your ass made it difficult to focus. You desperately wanted to feel his cock inside you, but he was rapidly rubbing you to an orgasm. He curled his fingers to hit that perfect spot inside your cunt and his thumb sped up, abusing your bundle of nerves in such a way that your thighs started to shake.

Just as you were about to cum, he withdrew his digits with an embarrassingly wet sound.

“Not yet,” he told you as he freed his dick from his briefs, letting the hard length slap against the small of your back where it left a wet smear of precum below the bunched up shirt.

His hand reached between your bodies and returned to your cunt, pushing your wet panties aside before placing his bulbous cockhead at your entrance. You didn't have time to tell him to get on with it, still teetering at the edge of orgasm, before he was already forcing himself into your tight channel. He bit your shoulder at the delicious friction surrounding his throbbing member.

The stretch burned, but Simon didn't give you any reprieve with his hand clamped around your hipbone while he kept pushing unforgivingly, only stopping once his impressive length was sheathed.

His breath came hard against your ear as he savoured the feeling of your clenching walls.

The pain of accommodating his girth eclipsed the pleasure for a brief minute before he started to grind into you and his thumb returned to your clit.

It took every ounce of control you possessed to not scream at the incredible friction his hard cock provided. You felt stuffed to the brim and were positive that you'd never had anyone as big as him, though the position might cause you to be even tighter than usual, making him feel massive.

His cock pressed into your G-spot as he swivelled his hips in a tantalising rhythm and before you knew what was happening, a blinding orgasm barrelled into you without warning.

Your back arched, impaling yourself even further on his cock. He bottomed out as your toes curled and a heatwave went through you, making your vision go white for a second. You couldn't have screamed even if you'd wanted to, your cry of release soundless in its intensity.

A light sheen of sweat covered your body, plastering the fine hair at your hairline against your temples and the back of your neck. As you slumped back against his muscled chest, feeling boneless in the wake of such exquisite pleasure, your walls kept fluttering around his dick.

His thumb had stilled after he'd pushed you over the edge, but now he resumed his agonising circles around your oversensitive clit as he started to thrust, making you buck involuntarily. The feathery touch was enough to set your nerves buzzing again.

“We ain't done yet. Yer didn't think I'd let yer off this easy, did yer?” he purred, pulling out until only his head was still inside before slowly hilting himself again, careful to keep the sounds of skin meeting skin to a minimum. “Now that I finally ‘ave yer, I'm gonna make it count. That's a promise, love.”

You weren't sure whether you wanted to move away from him or beg him to speed up, torn between pleasure and pain at the stimulation. Simon kept pumping into you with deep but measured thrusts, his thumb swiping across your nub every so often. He was coaxing you slowly but surely towards another climax, but this one felt like the slowest climb towards ecstasy you'd ever experienced. Ruthless in its inevitability.

Simon moaned into your ear, which sent shivers down your spine; his obvious arousal a huge turn on for you.

The hand covering your mouth went around your throat, restricting your breathing just enough to make you the tiniest bit light-headed.

God, how could he have known that to be one of your kinks?

The warm pressure combined with a particularly hard thrust that grazed your G-spot and nudged your cervix made your eyes roll back and elicited a long moan.  
Across from you, Dwight stirred, making the both of you suddenly freeze. Your eyes widened, praying that Dwight the Shite wouldn't turn around to face you. The adrenaline rush made your heart pound loudly.

Simon had stilled with his dick nestled deep within you and you thought you could feel his rapid heartbeat reverberating through his length pressed snugly inside you, matching yours.

After a few minutes, Simon began to grind his cock into you as his thumb drew hard circles onto your clit, making you quiver. Your gaze was still zeroed in on Dwight's back, afraid he might wake up any second and ruin this little nighttime adventure.

“Don't worry, Dwighty-boy wouldn't notice a bomb going off next to him,” Simon murmured before his hand squeezed your throat, drawing your attention back to what you were doing as his hand left your clit to grab your upper thigh.

He began to rock into you, slowing each time just before his hips could meet your ass as to not disturb the others. The last inch he pressed into you with a swivelling motion that had you seeing stars. That unfamiliar sensation drove you wild and managed to bring back your arousal with a vengeance as you once more found yourself rushing towards orgasm.

“Touch yourself,” he ordered.

Your shaky hand slid between your thighs to rub your clit with fast swipes, dragging the edge of your nail across the underside just so. Your cunt clenched around his invading length and you couldn't stop yourself from rolling your hips back into his punishing thrusts, writhing in pleasure.

“I'm gonna cum,” you squeaked.

“Not until I say so,” he growled. “Keep rubbing. But don't you dare cum without my permission.”

“I can't,” you pleaded. “Simon, please, I need to -”

“Don’t,” he bit out, increasing his pace. “Yer won't like what happens if yer disobey me.”

He wasn't exactly making it easy for you. His thrusts didn't slow down and the sloppy kisses he left from shoulder to ear only added to the fire threatening to consume you. The stench of sex made your brain go fuzzy and the noises your bodies were making as he surged into you stoked that fire to an inferno.

As the sensations heightened to the point of pain, the material of your borrowed shirt seemed to catch on your aching nipples and sweat trickled down your back, making the fabric cling to your spine. The brief thought of Simon reeking of sex and you on the ride home tomorrow almost made you snicker before you were consumed with the need to cum once more.

For the first time ever, you cursed a man's stamina. It was clear that he wouldn't let you get yours before he got his, but it was becoming impossible to stave off the climax that promised to eviscerate you.

“Now, dove. Cum for me,” he purred into your ear. “Cum on my dick.”

You didn't need any further encouragement. Pinching your clit, you finally let go, allowing the heat to envelope you. If the first orgasm had been white-hot silence, this once made you almost pass out as dark spots danced at the edges of your vision. You had to snap your neck to the side to bite into Simon's bicep in order to not scream the entire outpost down, barely registering his choked cry.

The continued strokes of his cock into your tight wetness only served to prolong your climax, but as you were slowly coming back down to earth, Simon's hips started to stutter. A few more rapid movements before he slammed into you and stilled. He exploded deep inside you with a strangled groan, pumping you full of his seed. Lazily riding out his high, he let go of your thigh and nuzzled into the side of your neck, chuckling.

“I should've dragged you into my bed sooner, love,” he teased hoarsely.

You couldn't even form words to reply or to tell him to withdraw. Your bones seemed to have dissolved entirely and you were barely able to feebly push against his hip, signalling to him that you were way too sensitive for him to stay seated with your limbs spasming periodically.

He got the hint and slowly extracted his limp cock from your well-used pussy. His seed dripped out of you, smearing across your inner thighs. Grabbing the blanket, he carefully cleaned you as much as possible. The thoughtful act made you smile.

Petting your hair before his hand cupped your chin to tilt your head for a sensual kiss, he murmured in pretend accusation, “You bit me.”

A weak laugh escaped you as he put his arm back around your waist to draw you flush against his chest.

“Yeah,” you breathed,” sorry, not sorry.”

You could feel the deep rumble of his laugh travel through his chest into your body. Entwining your fingers with his on your stomach, you swiftly fell into an exhausted, but sated, sleep.


End file.
